Lewis acid-mediated Suzuki–Miyaura Cross-Coupling Reaction

Abstract

The palladium-catalysed Suzuki–Miyaura cross-coupling (SMC) reaction of organohalides and organoborons is a reliable method for carbon–carbon bond formation. This reaction involves a base-mediated transmetalation process, but the presence of a base also promotes competitive protodeborylation, which reduces the efficiency. Herein, we established an SMC reaction via Lewis acid-mediated transmetalation of an organopalladium(II) intermediate with organoborons. Experimental and theoretical investigations indicate that the controlled release of the transmetalation-active intermediate enabled base-independent transmetalation under heating conditions and enhanced the applicable scope of this process. This system enabled us to avoid the addition of a base, and thus, rendered substrates with base-sensitive moieties available. Results from this research further expand the overall utility of cross-coupling chemistry.

Aryl Dance Reaction of Arylbenzoheteroles

“…Furthermore, the addition of phenylboronic acid, a palladium catalyst, and a zinc catalyst after the addition of NBS allowed the Suzuki−Miyaura coupling reaction to proceed, yielding diarylbenzothiophene 8. 10 The structure of the obtained 8 was determined by X-ray analysis after recrystallization. It was also possible to react bromobenzothiophene 9 in arylation and aryl dance reactions in a one-pot process (Scheme 3C).…”